Yesterday afternoon I spent a fair amount of time replying to an e-mail from a man who wrote to tell me that he was tired of his corporate job and wanted to become self-employed. So far, so good.

Then he went on to give me all the reasons why this was impossible. He had a large family to support, he was too exhausted when he got home from work to get something going, etc. etc. There wasn’t anything very original about his list.

I wrote back and said, “Just from what you told me, I think you may be getting ahead of yourself. Of course, it seems overwhelming to make a life transition when you’re already booked and committed.

“Do you have a clear idea about what sort of business you’d like to start? Can you find even 30 minutes a day to start laying the groundwork? Have you got written goals? Can you get family support for making a lifestyle change? Seems to me, your next step is to plan your transition…not decide it can’t be done.”

What I wanted to tell him, but didn’t, was that he called to mind Richard Bach’s observation: “Argue for your limitations and, sure enough, they’re yours.”

I had barely hit the send button on my message when my phone rang. The call was from Paul, a man I’d met several years ago when he attended my seminars in San Francisco.

At the time, Paul was working at a government job, not so happily married, and longing to travel. I remember how somber and sad he seemed.

When I heard from him next, he had quit his job, left his bad marriage and was focusing on making his living from travel.

It was fun to watch as Paul began building his business teaching various travel seminars he’d created. At first, he focused on teaching in his home state of California. The next year he went national and was zipping around the country sharing information on living abroad and getting the most out of traveling like a local.

When Paul’s parents became ill, he suspended his travel activities to care for them. In the past year, both his mother and father had died and Paul is planning his next chapter.

He told me about his immediate plans to study French in Montreal and spend time on a Semester at Sea.  As he was sharing his excitement about his new adventures, I kept thinking about my e-mail correspondent who felt so trapped.

Cynics would point out that Paul does not have the same obligations as the other fellow so, obviously, he can gallivant around. Cynics would be missing the point.

In our long catch-up chat, Paul told me that he really didn’t have any long-term plans. He was focusing on his upcoming travels. “I’m not worried. Having the experience of starting my business gave me so much confidence,” he said, “that I know I can do it again.”

It’s an observation I’ve heard over and over again from my self-employed friends. Why then, I wonder, is Paul’s discovery such a well-kept secret? And why do so many people treat self-employment like a spectator sport?

Maybe the answer to those perplexing questions can be found in these words from an anonymous source: A willing heart will find a thousand ways. An unwilling heart will find a thousand excuses.

Or perhaps Paul has discovered what Chris Rock pointed out in an interview last week on CBS Sunday Morning. “Being rich is not about having a lot of money,” Rock said. “Being rich is about having a lot of options.”


Author Bill Bryson talks about being on a train and thinking about fellow travel writer Paul Theroux writing about the fascinating conversations he has with strangers. This seemed to perplex Bryson because he found it difficult to strike up conversations with traveling Brits.

That got me thinking about a short conversation with an enthusiastic traveler who confessed that he found it difficult to talk to strangers and wondered how I did it.

Since my Do Talk To Strangers Policy is a vital component of traveling—and being entrepreneurial—I started to consider how I actually go about it. I realized that some of it is purely intuitive.

For instance, when a stranger plunks down next to me on an airplane, I take a breath, take a look and see if I’m moved to start a conversation. Most of the time I get it right. Once in a while, I know  from my opening question that my seatmate is inclined toward solitude and I stop there.

Whether you’re standing in line at the post office or waiting for a train, here are a few ideas to help you uncover the fascinating folks around you.

° Make it a game. Decide ahead of time that you want to find an interesting story or inspiring stranger. I have been on long flights that seemed to pass in a moment  because I had landed next to a great storyteller. I consider that a fine compensation for the annoyances of contemporary travel.

° Don’t wait. Instigate. Be willing to be the one who takes the first step. A friendly smile is a good way to test the water. If it’s not reciprocated, move on.

° Look for common ground. I often open a conversation with a compliment or observation about something the stranger is wearing or carrying or something that’s happening around us.

When I hopped into a London taxi that was covered in promotional material for the Rolling Stones, I suspected I had a fascinating chat ahead of me. And I did.

I learned that my driver was the only cab in the city promoting the Stones, that he earned an extra £750 a year by putting advertising on his cab, and that he’d once advertised for the South African Tourist Board and got a free trip to that country as a bonus. He was hoping he might get tickets to a Stones concert this time around.

° Be politely curious. Our reluctance to talk to strangers may be caused by thinking it’s about us. Wrong. It’s about them. Yes, you might be subjected to a tedious story now and then, but it’s worth the risk.

One of my most memorable conversations was with a young man who was a linguistic professor who spoke seven languages. When I learned that, I asked him the best way to learn a language and his reply was, “Be a kid.” I laughed and asked, “What’s the second best ?”

The answer to that question—and many more—kept us chatting from Minneapolis to Los Angeles. I learned a lot and enjoyed his willingness to share his linguistic passion.

Those are the moments that keep me talking to strangers who unknowingly enrich my life.  And like everything else, it gets easier with practice.



I’ve been going through 25 years of back issues of Winning Ways newsletter to gather my favorite articles that I’m collecting for an e-book. I came across this one from 1990 and thought it was worth sharing here as well.

“April is the cruelest month,” mused T.S. Eliot. Obviously, he wasn’t around in October. While the weather had been magnificent, many people were not so inclined. For background noise there was the nightly news with an unrelenting stream of stories about war, recession and political nastiness.

Closer at hand were the two women who left their manners at home when they came to my English tea class and the burglar who removed the battery from my car.

Staying positive in a negative world is challenging even in normal times, but this felt as if guerilla tactics were in order. Here are some of the most helpful I’ve found for getting past negative times and creating positive ones.

° Bombard yourself with positives. Overcompensate. Sondra Ray has a wonderful affirmation that goes, “Every negative thought immediately triggers three more powerful positive ones.”

If things are looking dim, consciously create the opposite thought. Keep your favorite books of inspiration close at hand and read at random during crisis moments.

° Take a proactive stance—and keep it. Nobody does a better job of explaining proactive vs. reactive behavior than Stephen Covey.

In his classic The 7 Habits of Highly Effective People he writes, “Proactive people focus their efforts on the things they can do something about. The nature of their energy is positive, enlarging and magnifying causing their circle of influence to increase.

“Reactive people, on the other hand, focus on the weakness of other people, the problems in the environment, and circumstances over which they have no control. Their focus results in blaming and accusing attitudes, reactive language and increased feelings of victimization.”

If you need more information about moving into a proactive position, revisit Covey’s book for practical suggestions.

° Indulge a passion. One year, I created two challenges for myself: to discover all the ways that chocolate and raspberries could be combined and to see all of the Monet paintings I could with my own two eyes. Both of these quests added hours of pleasure when I was traveling—and when I was not.

I highly recommend you give yourself a similar challenge.

° Catch someone doing something right and let them know. I noticed a woman at the airport in Chicago wearing a smart outfit. When she reappeared in Minneapolis, I walked up to her and told her I’d been admiring her clothes. She thanked me and said, “You can probably tell by my accent that you’d have to go a long way to get one for yourself.”

“Where are you from?” I inquired. When she told me London was her hometown, I said, “Oh, but I’m going there next month!”

I came away with a warm feeling and a great shopping tip.

° Take yourself on a mini-retreat. Sometimes the only way to diffuse negative energy is to move yourself completely out of it. So plan a day or two doing something you normally wouldn’t do.

Spend Wednesday doing the Sunday crossword. Watch the seasons change at a cabin at the lake. Have a massage at bedtime.

While you are so engaged, concentrate fully on what’s going on in front of you—not the situation that upset you in the first place.

° Discover the hidden gift in the problem. When my car was burglarized, I was mighty upset. Then one of the handsomest men I have ever met arrived at my door (wearing his police uniform) and things began to look a bit brighter.

We even managed to laugh about the situation when he asked me to check the car for further theft. I looked around and told him all of my music CDs were in place. “I don’t suppose that people who steal batteries would steal Mozart, would they?” I asked.

Negative times can be profoundly diminished if you have tools for dealing with them.

Abraham Maslow once described the self-actualized person’s response to chaos by saying they behaved “like a clock ticking in a thunderstorm.” It’s a picture I’ve tried to remember in crazy times and attempted to duplicate.

None of us is immune to life’s negative events, but it’s possible to minimize their impact. In the end, it’s really a matter of learning to starve our upsets and feed our opportunities.


“Fun is fundamental,” Sir Richard Branson reminds us. That’s the antithesis of all those business mottos which sound more like Fun is Forbidden.

How can you earn money by having fun? There are numerous ways, but the essential thing is to begin by creating a business that’s so much fun for you that you can’t wait to get at it every morning.

Then you can heighten the fun—and build your entrepreneurial thinking—by creating small projects where you get paid to do things you find pleasurable. The trick is to take a creative approach and uncover new funding pleasures. You won’t get rich with any of these ideas, but your life will be noticeably richer in fun.

Do You Love…

° Working out? Check with your health insurance provider and see if they offer a financial reward if you take care of yourself. Mine gives a $20/month discount on their premiums to anyone who goes to the gym eight times a month.

°  Classical music? Usher at your symphony hall and get paid to listen. The same goes for theater and other entertainment venues. Sometimes these are volunteer positions and sometimes they pay a small salary.

• Having a massage? Schools of massage need bodies to practice on and sometimes they even pay to use yours. Other programs offer free or almost free massages for those willing to be part of the curriculum.

Then there’s the woman who evaluates spa services for a hotel chain. That’s an idea that could be turned into an independent business.

° Giving your opinion? Sign up with local marketing agencies that put together focus groups to evaluate new products. Everything from frozen food to legal services get evaluated by focus groups.

I once participated in a focus group for an airline and we were pleasantly surprised at the end of the session to learn we could be paid $70—or receive two roundtrip tickets to Europe on the carrier.

° Shopping? Mystery shopping companies hire people to evaluate employees and service in businesses. The mystery shopper poses as a customer and then files a report on the transaction. I once got a new muffler installed in my car this way.

Not all shops are exciting, but if you like dining out or going to the mall, why not get paid for it? Make sure you’re working with a legitimate operation.

° Research? Ah, those closet detectives among us are the folks who love digging deeply into a subject. Besides creating a business that does other people’s research for them, there’s another fun possibility: creating an independent research project and then getting it funded.

The reference section of your local library will have directories of grant opportunities. Also helpful to the nonacademic grantseeker is The Complete Guide to Getting a Grant by Laurie Blum. This book has been around for a while, but the information is still valid.

° Travel? Of course, I have dozens of suggestions for getting paid to travel in my How To Support Your Wanderlust seminar. One of those ways is to organize a tour. Special interest tours work best for the independent organizer.

I met two delightful women from Australia at a restaurant in London who told me about a tour they’d taken to the US to visit quilting museums and workshops. They were on another special interest tour on their UK trip.

If you have a passion you love sharing with other people, find a company that specializes in group travel to help you put the tour together.

Use this Money for Fun exercise to wake up your imagination to new possibilities. The options are endless, but not automatic.

You could challenge yourself to think of five fun activities that you truly enjoy, but normally pay to participate in. Start exploring ways of being paid instead of paying. Coming up with new options will be as good for your imagination as it is for your pocketbook.





Years ago when I lived in Santa Barbara, I observed a weekly ritual—the Friday migration north which was followed by the Sunday migration south. I’ve often wondered if such traffic jams inspired Loverboy’s Working for the Weekend.

For too many of us, work and fun have occupied separate territories.  In my family, there was a frequently quoted German adage that translated to “first you work, then you play.” The implication was that never the twain shall meet.

No adults I knew growing up suggested that I should discover what brought me joy before I began to think about choosing a career—and I certainly didn’t see many folks who seemed to be having a great time going about their work.

When I realized that I would be spending a huge amount of time working, an occasional fun weekend didn’t seem a fair tradeoff for days of drudgery. Although it was done in private, I began my own Joy Quest to see if I could get paid to have fun.

Along the way, I heard Moneylove author Jerry Gilles say, “Anything worth having is worth having fun getting.” It seemed like an idea worth testing. I decided to go for joy all along the way.

Some of the things I discovered were downright startling. I found that as my own boss, with a new vision to create, I could tackle things on behalf of building my own business that would have driven me crazy had I been doing them as part of a job.

Working with joy seemed to spill over to activities I might previously have dreaded. For instance, if someone had handed me thousands of newsletters to label and stamp, I’d have tensed right up, but when that pile is Winning Ways, and I’ve put it together myself, I can’t wait to share it with my subscribers.

When our work is also a source of joy and fun, it leads us to become more creative, more engaged, more masterful. Those rewards are much harder to obtain when we’re only working for money.

So during March, we’ll be exploring the theme of Money for Fun. I’d love to hear your stories about the most fun you’ve ever had earning money. Since I made that request in the last Joyfully Jobless News, people have been sending me delightful examples which I’m going to be sharing throughout the month, but I’d love more inspiring tales.

As poet David Whyte reminds us, “Anyone or anything that does not bring you alive is too small for you.”

I’m pretty sure that includes work.

Several years ago I decided to start a list of things I loved doing so much I could do them every day without getting bored. I wanted the list as a reminder to integrate beloved activities and things on a daily basis.

I thought of that this morning as I was driving home from yet another visit to the DMV and heard one of Bach’s Brandenburg Concertos, one of the things that made my Everyday Love List.

It’s not just the music I love, however. I also love the story. Those lovely pieces were written for a competition held by the city of Brandenburg-Schwedt, Germany. It was a competition won by somebody else.

Nobody seems to remember winner’s name, nor his musical entry, but Bach’s concertos frequently top the list of public radio listener’s favorites 290 years after they first were played.

Today I was also reminded that even onerous tasks can be more pleasant if we include things we love. It doesn’t do much good, after all, if we know what we love, but don’t have regular contact with them.

A while back, Alice Barry and I had a conference call with participants who had attended our Follow Through Camp retreat. I asked everyone to complete an exercise before the call.

This fun idea comes from Keri Smith’s delightful book, Living Out Loud . It’s called Lifestyle for Sale and it goes like this:

In recent years, lifestyle stores have become the rage, selling products related to all aspects of living: eating, decorating, reading, bathing, sleeping and dressing. If you were to open your own lifestyle store, what would you sell?

Make a list of what it would contain. What items best represent you and your many layers? Are they eclectic? Chaotic? Minimal? Calming?

Come up with a name for your store—maybe it’s a character from your favorite book, or something that reflects the store’s contents.

Before the call, I  also created my own imaginary lifestyle store. Like many of the other callers, I envisioned my store in a funky old house reached by walking through a garden.

My store wasn’t just about stuff, but also about stuff happening. There was a conservatory on the back called the Idea Factory for collaborative brainstorming. Another spot was called the Follow Through Room where people who felt stuck could find inspiration and support to get moving again.

The bookshop section had four distinct sections, each housed in a separate corner. One was devoted to personal growth, another to biographies of kindred spirits, another on business building and another on supporting wanderlust.

Every room was furnished with big, comfy chairs and vintage travel posters adorned the walls. Happily, the place where I live resembles my imaginary store.

Although none of the folks who did this with Alice and me were interested in opening a shop, creating this vision got them dreaming about spending time in the kind of place they’d imagined.

It’s a great exercise and I urge you to try it yourself. More importantly, surround yourself with people, things, and ideas you love as much as you possibly can.

As the John Ruskin poster in my office never lets me forget, “We are not sent into this world to do anything which is not in our hearts.”

Of course, first we need to know what that is.

While I was waiting (and waiting) for UPS to show up with Winning Ways newsletters, I decided to tackle the grungy grout in my tiled entrance. I’m a bit of a fanatic about dirty grout after spending five years in a house with tiled floors in dusty Las Vegas.

(Bonus tip: To clean grout, make a paste of baking soda and peroxide and apply with a battery operated toothbrush. Let stand for a few minutes and mop up.)

As I was polishing, I got thinking about how important it is for me to have a home that welcomes me and others. In fact, one of the first purchases I made for my new condo was a welcome mat that’s covered with bright red and purple flowers.

Everytime I return home and see it, it makes me smile and silently affirm, “I welcome my good.”

It’s a stunning contrast to the doormat outside my downstairs neighbor’s home which declares, “Go Away.” I haven’t met the owner of that place, but I’ve tried to imagine why they choose to make that statement to passersby.

Perhaps it was a housewarming gift that was intended as a joke, I mused. Or maybe they are weary of chasing away paparazzi. Of course, there’s also the possibility that they’re truly anti-social and proud of it.

What kind of welcome mat are you putting out? The way you answer the phone, the ease of navigating your Web site, the speed with which you answer e-mail, the extra effort to right an error, all communicate Welcome or Go Away.

This morning my local public radio station had a lively conversation about annoying background music in stores. Caller after caller talked about being driven out of retail establishments by loud music.

You may have had the same experience.

One woman said she’d accompanied a friend to an emergency animal hospital on the night her friend’s cat had to be put to sleep. They arrived at the hospital and found the waiting room television running a raucous comedy program. “It seemed insensitive,” she said.

It’s easy when we’re busy or distracted to ignore small courtesies, but it’s worth the time and energy to consider how to be as welcoming as possible.

Think of it as regularly scrubbing the grout. Then top it off with the most cheerful welcome mat you can find because, whether we realize it or not, we’re all in the hospitality business.

There are hundreds of perfectly smart reasons to be Joyfully Jobless, not the least of which is that people who are doing work that they love tend to be, well, more loving and joyful.

One time after I’d visited my aunt Marge, she sent me a letter that said, “The Bible says a merry heart doeth good like a medicine. That’s how I feel when you come to see me.”

Besides that fact that it was one of the nicest letters I ever got, it’s remained a powerful reminder of why it’s important to stay merry. Here are some of my favorite ways to bring more fun and joy into a business.

° Specialize in Firsts. Challenge yourself to do things you’ve never done before. It can be as simple as trying a new food or taking a yoga class.

This is harder to do than you may think since we humans tend to build habits and then operate in familiar territory. Having Firsts requires conscious, creative effort.

° Exercise your entrepreneurial thinking to keep it in shape. You build entrepreneurial muscle by studying other enterprises, by acquiring new skills, by taking risks.

Just like physical exercise, it needs to be a daily activity if you want maximum results.

° Don’t be afraid to be whimsical. Small businesses should not look like miniature corporations.

Lighten up. Create a costume and wear it when you work or exhibit at a trade show. Have toys or a guitar in your office for play breaks.

And if whimsy’s not your style, from time to time purposely do something out of character. You’re bound to startle your friends and you might delight yourself.

° Celebrate all victories. Jim Rohn told a story about his early days in business and how he’d take his family out for dinner and say, “Tonight we’re ordering from the left side of the the menu. Pay no attention to prices.” He said it helped him stay on track.

Find your own way to celebrate milestones and progress. Send yourself flowers or invite a friend on an outing. Don’t let victories—large or small—go unnoticed.

° Plan Joyfully Jobless get togethers. Find 5 other self-bossers that like each other and let each one plan a monthly gathering, just to have fun.

You could find yourself salsa dancing one month and picnicking in a park the next. Hanging out with other entrepreneurs can be a lovely tonic, but don’t wait for somebody else to get things rolling.

° Turn ordinary chores into satisfying rituals. Got bills to pay? Instead of gritting your teeth, light a candle, put on some lovely music, pour a cup of tea and make it an event. Slow down and express gratitude for your current abundance.

Invent rituals to turn ordinary tasks into something special.

° Stay focused on rewards. On snowy days in Minnesota, my Joyfully Jobless friends and I would call each other to rejoice that we didn’t have to drive on bad roads.

Keep a running list of all the rewards that you enjoy because you’re self-employed. Post it in your workspace and remind yourself often of the benefits and pleasures of this lifestyle.

° Support that which supports you. This has been my personal and business policy for a long time and it hasn’t failed me yet.

For example, I give top priority to supporting the self-bossers who support me. My newsletter, Winning Ways, is designed to pass along ideas and resources that have helped me on my journey.

You get the idea.

° Expect the unexpected. Businesses often surprise us with new opportunities and directions. While this may be upsetting to control freaks, true entrepreneurs delight in it.

° Change the scenery. The creative spirit flourishes when exposed to new people and places.

Whether that means taking your laptop to the park for a morning writing session or attending a weekend seminar, give yourself the benefit of working in different ways. Rigid routine is the enemy of creativity.

° Be kind. When we commit an act of kindness our endorphin level goes up. Likewise, when we receive a kindness it raises our levels.

However, studies have also found that if we merely witness an act of kindness, it raises endorphin levels too.

Go ahead and spread some kindness around.

Either you run the day or the day runs you;

either you run the business or the business runs you.

Jim Rohn

Although self-bossers are quick to realize that having control of their own time is one of the great rewards of self-employment, using time wisely may be a new skill we need to acquire since most of us have spent a fair amount of time following schedules set by others who told us when to arrive at class, the office or the dinner table.

Go For Balance

Travel writer Rick Steves says, “When you let your time become money you cheapen your life. One measure of a culture is its treatment of time. In the United States time is money: we save it, spend it, invest it and waste it.”

This can be a difficult attitude to get over, but the key may not be to manage our time, but to balance our lives.

“Whenever our schedules become disproportionate, our energy drops,” Doreen Virtue points out. “Lowered energy creates the illusion that there isn’t enough time in the day, so a vicious cycle of time limitation ensues….Balancing your life between work, play, spirituality, exercise, and relationships helps you to grow and feel joy.”

Being self-employed gives us a head start in creating the balance Virtue talks about.

Check Your Priorities

It’s only with regular and frequent reviewing of our priorities that we can create a life that reflects what we value most. Otherwise we get swept along by chores, tasks and the demands of others.

In his book How To Get Control of Your Time and Your Life, Alan Lakein shares his simple method for setting priorities on a daily basis.  Once you’ve written down your To Do List, you give each item an A, B, or C rating.

A items are the most important; B items are those you’ll get to if the A items get done; C items may just be busy work. Eventually, C items disappear altogether as we focus on our most important activities.

Sometimes our true priorities dictate that we be obsessive about a single task until it is done. At other times, our priorities may be to have lots of variety of activities in our day.

The important thing is to know what truly matters and then set up each day to reflect that.

60 Minutes did a story that illustrated how little attention is given to creative idleness. The piece was a study of the young people known as Echo Boomers, children of the Baby Boom generation. Now reaching their late teens, this group has grown up with jam-packed schedules and endless encouragement to be team players. Sadly, many of these kids are at a loss given unscheduled time on their own.

Staring out a window or walking in a woods is not necessarily the sign of a slacker. Writer Anna Quindlen concurs.

She says, “Downtime is where we become ourselves. I don’t believe you can write poetry, or compose music, or become an actor without downtime and plenty of it, a hiatus that passes for boredom but is really the quiet moving of the wheels inside that fuel creativity.”

Successful entrepreneurs master the fine art of woolgathering.

So don’t ditch your Day Planner or Palm Pilot, but do give attention to alignment, balance and creativity in arranging your moments.

After all, you put yourself in charge when you decided to go after a dream and only you can decide if you’ll move closer or farther away minute by minute by minute.

Comedian Paula Poundstone once said, “My father always told me I needed something to fall back on. But I knew if I listened, I’d fall back.”

I thought of that this morning when I read Connie Hozvicka’s blog post about that very thing.

Connie, who did a pair of marvelous workshops at the Joyfully Jobless Jamboree, is brand new to the Joyfully Jobless life. Like most of us, she’s had to challenge some not-so-helpful conventional wisdom.

What creative person hasn’t been told You Need Something To Fall Back On? Read Connie’s take on it here.

Here are ten other bits of wisdom that haven’t been widely circulated. It’s my personal list of things self-employment teaches me each and every day.

1. To think creatively and see that there are opportunities to approach the most ordinary tasks in creative ways.

2. To be an enthusiastic problem-solver.

3. It’s okay to be uncomfortable. In fact, comfort zones are much scarier.

4. Expanding is more fun than shrinking.

5. Right livelihood alters the way we think about work.

6. We can be more, do more, have more than we originally thought possible.

7. Imagination is a power tool.

8. If we ask better questions, we get better answers.

9. Personal responsibility is heady stuff.

10. Lifelong learning is a joy.

“There’s an unexpected pleasure attending the life of a voluntary student,” said Oliver Goldsmith. I think he was talking about us.